Figure 6: Proposed mechanism for the formation of six-membered ring. | Nature Communications

Figure 6: Proposed mechanism for the formation of six-membered ring.

From: Synthesis of tetrasubstituted 1-silyloxy-3-aminobutadienes and chemistry beyond Diels–Alder reactions

Figure 6

(a) For the isotope experiment, dichloromethane was shaken rigorously with H218O and subsequently used for the reaction. (b) The enamine functionality is the primary reason for the facile conversion of the CF3 group to the carbonyl, as it pushes an electron pair towards CF3 and triggers the elimination of a fluoride anion. The alkyne moiety is also believed to be important for stabilizing the adjacent enamine.

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